From the day she started working at the Defense Intelligence Agency in 1985 until the day she was arrested for conspiracy to commit espionage in 2001, Ana Montes was a spy working on behalf of Cuban Intelligence. On this episode of DIA Connections, we examine the nefarious activities of this highly decorated intelligence analyst who became one of the most damaging spies ever caught engaging in espionage against the United States. Conversations with a counterintelligence investigator, a spy psychiatrist and bestselling author Malcolm Gladwell, help to unravel the challenges and pitfalls in catching the woman known as the “Queen of Cuba”.